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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 12: 4220 - 4226

DOI: https://doi.org/10.6023/cjoc202304033

ARTICLES

N-Iodosuccinimide-Promoted Cascade Oxoazidation of Alkenyl Oximes: Synthesis of Azido Isoxazolines

  • Haoran Liu ,
  • Junhao Yu ,
  • Tongyang Cao ,
  • Lin Qi ,
  • Lijing Wang
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  • a College of Chemistry and Materials Science, Hebei University, Baoding, Hebei 071002
    b Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, Baoding, Hebei 071002
†The authors contributed equally to this work.
*E-mail: ;

Received date: 2023-04-25

  Revised date: 2023-07-17

  Online published: 2023-08-15

Supported by

National Natural Science Foundation of China(21702043); Hebei Province Natural Science Foundation(B2021201035)

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Abstract

A N-iodosuccinimide (NIS)-promoted cascade oxoazidation of alkenyl oximes with NaN3 was developed, and a series of azido isoxazoline derivatives were synthesized in good yields. The reactions are easy to be conducted under mild conditions. The mechanism study shows that the reaction might involve a cascade electrophilic iodocyclization/nucleophilic substitution pathway.

Key words： N-iodosuccinimide (NIS); alkenyl oximes; oxoazidation; isoxazolines

Cite this article

Haoran Liu , Junhao Yu , Tongyang Cao , Lin Qi , Lijing Wang . N-Iodosuccinimide-Promoted Cascade Oxoazidation of Alkenyl Oximes: Synthesis of Azido Isoxazolines[J]. Chinese Journal of Organic Chemistry, 2023 , 43(12) : 4220 -4226 . DOI: 10.6023/cjoc202304033

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